Alternatived Products of [ 1369143-28-1 ]
Product Details of [ 1369143-28-1 ]
| CAS No. : | 1369143-28-1 |
MDL No. : | MFCD22034498 |
| Formula : |
C9H5BrO3
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | AWHJIEGQJDBVCF-UHFFFAOYSA-N |
| M.W : | 241.04 |
Pubchem ID : | 67202761 |
| Synonyms : |
|
Safety of [ 1369143-28-1 ]
Application In Synthesis of [ 1369143-28-1 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 1369143-28-1 ]
- 1
-
[ CAS Unavailable ]
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[ 1369143-28-1 ]
-
[ 26028-36-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 76% |
With thionyl chloride at 0 - 60℃; for 4h; |
1 Step-1: Methyl 5-bromobenzofuran-2-carboxylate
To a solution of 4-bromobenzofuran-2-carboxylic acid (0.5 g, 2.1 mmol) in Methanol (10 mL) was added, SOCl2 (0.2 mL, 3.1 mmol) at 0 °C drop-wise and the reaction mixture was heated to 60 °C for 4 h. After completion (TLC), it was concentrated and diluted with ice cold water. The aqueous layer was extracted with Ethyl acetate (3 X 10 mL), washed with water, dried and concentrated under reduced pressure to give titled compound (0.4 g, 76%). Step-2: Methyl 5-(4,4,5,5-tetrameth l-l,3,2-dioxaborolan-2-yl)benzofuran-2-carboxylate |
- 2
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[ 1369143-28-1 ]
-
[ 1820715-36-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: thionyl chloride / 4 h / 0 - 60 °C
2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 100 °C / Sealed tube |
|
- 3
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[ 517-89-5 ]
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4-bromobenzofuran-2-carboxylic acid
[ No CAS ]
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(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 4-bromobenzofuran-2-carboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 30.2% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 8h; |
4.1.3 Synthesis of compounds 6a-6q
General procedure: Shikonin (1mmol), benzofuran-2-carboxylic acid derivatives (4a-4q) (3mmol), 4-dimethyaminopyridine (0.5mmol), and N, N′- dicyclohexylcarbodiimide (0.5mmol) were suspended in the anhydrous DCM (10ml). The reaction mixture was stirred for 8h under 0°C. Afterwards, the targeted compounds 6a-6q were purified by column chromatography. |
- 4
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[ 177735-22-7 ]
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[ 1369143-28-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydroxide In water; N,N-dimethyl-formamide at 60℃; for 0.5h; |
General procedure: To a solution of intermediates 3a-3q (1mmol) in 10ml DMF, 2.0mL of 20% sodium hydroxide solution was dropped at 60°C to carry out the ester hydrolysis reaction for 30min. Afterwards, the mixture was cooled to room temperature, and the PH value of the solution was adjusted to 2 using 10% hydrochloric acid, then the mixture was extracted with ethyl acetate. The organic phase was combined and condensed by vacuum concentration to afford the crude product, which was purified by recrystallization to give the designed compounds (4a-4q). |
- 5
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[ 2411697-65-7 ]
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[ 1369143-28-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 120 °C
2: sodium hydroxide / N,N-dimethyl-formamide; water / 0.5 h / 60 °C |
|
- 6
-
[ 22532-61-2 ]
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4-bromobenzofuran-2-carboxylic acid
[ No CAS ]
- 7
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[ 1369143-28-1 ]
-
[ 2779558-91-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine / 2.67 h / 20 - 95 °C
2: tetrahydrofuran / 2 h / -78 °C |
|
- 8
-
[ 1369143-28-1 ]
-
[ CAS Unavailable ]
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[ 2779558-90-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 66% |
With diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine at 20 - 95℃; for 2.66667h; |
6 Zc/V-Butyl N-(4-bromobenzofuran-2-yl)carbamate
A mixture of 4-bromobenzofuran-2-carboxylic acid (1.00 g, 4.15 mmol), diphenylphosphoryl azide (1.34 mL, 6.20 mmol), and DIEA (1.09 mL, 6.25 mmol) in Zc/V-butyl alcohol (12 mL) is stirred for 10 minutes at ambient temperature before heating to 95 °C. After 2.5 hours, the heat is removed and the solvents are removed in vacuo. The resulting residue is purified via silica gel flash chromatography eluting with 0-50% EtOAc/hexane to give the title compound as a white solid (850 mg, 66%). ES/MS m/z (79Br/81Br) 255.6/257.6 [M-t-Bu+H]+ |
| 66% |
With diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine at 20 - 95℃; for 2.66667h; |
6 Zc/V-Butyl N-(4-bromobenzofuran-2-yl)carbamate
A mixture of 4-bromobenzofuran-2-carboxylic acid (1.00 g, 4.15 mmol), diphenylphosphoryl azide (1.34 mL, 6.20 mmol), and DIEA (1.09 mL, 6.25 mmol) in Zc/V-butyl alcohol (12 mL) is stirred for 10 minutes at ambient temperature before heating to 95 °C. After 2.5 hours, the heat is removed and the solvents are removed in vacuo. The resulting residue is purified via silica gel flash chromatography eluting with 0-50% EtOAc/hexane to give the title compound as a white solid (850 mg, 66%). ES/MS m/z (79Br/81Br) 255.6/257.6 [M-t-Bu+H]+ |
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